3-Phenyl substituted 3-substituted-4ketolactams and ketolactones

ABSTRACT

The invention relates to novel 3-phenyl-substituted, 3-substituted 4-ketolactams and -lactones of the formula (I)  
                 
in which Q, W, X, Y, A, B and G are as defined in the disclosure, to processes and intermediates for their preparation and to their use as pesticides and herbicides.

The invention relates to novel 3-phenyl-substituted, 3-substituted4-ketolactams and -lactones, to processes and intermediates for theirpreparation and to their use as pesticides and herbicides.

It is already known that certain phenyl-substituted 3-halo-4-ketolactams(JP-A-10-258 555) and phenyl-substituted 3-halo-4-ketolactones(JP-A-10-258 555) act as acaricides or insecticides and/or herbicides.

However, in particular at low application rates and concentrations, theactivity and activity spectrum of these compounds is not always entirelysatisfactory. Furthermore, the compatibility of these compounds with thecrop plants is not always sufficient.

This invention now provides novel compounds of the formula (I)

in which

-   Q represents oxygen or N—H,-   W represents alkyl,-   X represents hydrogen, halogen or alkyl,-   Y represents halogen or alkyl,    -   with the proviso that at least one of the radicals X or Y        represents halogen,-   A represents haloalkyl, alkyl, alkoxyalkyl, benzyl or optionally    substituted cycloalkyl,-   B represents hydrogen or alkyl,-   A and B together with the carbon atom to which they are attached    represent a saturated, optionally alkyl- or haloalkyl-substituted    cycle,-   G represents halogen or nitro.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) can be present as geometrical and/or optical isomers orisomer mixtures of varying composition which, if appropriate, can beseparated in a customary manner. The present invention provides both thepure isomers and the isomer mixtures, their preparation and use andcompositions comprising them. However, hereinbelow, for the sake ofsimplicity, compounds of the formula (I) are always referred to,although this is meant to include both the pure compounds and, ifappropriate, mixtures having varying proportions of isomeric compounds.

Including the meanings of Q, the following principal structures (I-1) to(I-2),

result, in whichA, B, G, W, X and Y are as defined above.

A) Furthermore, it has been found that compounds of the formulae (I-1)to (I-2)

-   -   in which A, B, Q, W, X and Y are as defined above and    -   G represents halogen, preferably chlorine and bromine,    -   are obtained when compounds of the formulae (II-1) to (II-2)    -   in which A, B, Q, W, X and Y are as defined above    -   are reacted with halogenating agents in the presence of a        solvent and, if appropriate, in the presence of a free-radical        initiator.

B) Furthermore, compounds of the formulae (I-1) to (I-2)

-   -   in which A, B, Q, W, X and Y are as defined above and    -   G represents nitro,    -   are obtained when compounds of the formulae (II-1) to (II-2)    -   in which    -   A, B, Q, W, X and Y are as defined above    -   are reacted with nitrating agents, such as, for example, fuming        nitric acid, in the presence of a solvent.

Some of the compounds of the formulae (II-1) to (II-2)

in whichA, B, Q, W, X and Y are as defined above,which compounds are required for processes A and B, are known compounds(for example from EP-A 668 267, WO 96/35 664, WO 97/02 243), or they canbe synthesized by the processes described therein.

Suitable halogenating agents for process A are, for example, sulphurylchloride, sulphuryl bromide, thionyl chloride, thionyl bromide, imides,such as, for example, N-bromosuccinimide or N-chlorosuccinimidechlorosulphonic acid, and also hypochlorites, such as, for example,tert-butyl hypochlorite.

Suitable nitrating agents for process B are fuming nitric acid, and also“nitrating acid mixtures”.

Furthermore, it has been found that the novel compounds of the formula(I) have very good activity as pesticides, preferably as insecticidesand/or acaricides and/or herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below:

-   Q preferably represents oxygen or N—H,-   W preferably represents C₁-C₄-alkyl,-   X preferably represents hydrogen, halogen or C₁-C₄-alkyl,-   Y preferably represents halogen or C₁-C₂-alkyl,    -   with the proviso that at least one of the radicals X or Y        represents halogen,-   A preferably represents C₁-C₈-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl, benzyl or represents C₃-C₆-cycloalkyl    which is optionally mono- or disubstituted by C₁-C₄-alkyl,    C₁-C₄-alkoxy or halogen,-   B preferably represents hydrogen or C₁-C₄-alkyl,-   A, B and the carbon atom to which they are attached preferably    represent saturated C₃-C₈-cycloalkyl which is optionally mono- or    disubstituted by C₁-C₄-alkyl or C₁-C₂-haloalkyl,-   G preferably represents chlorine, bromine or nitro.

In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   Q particularly preferably represents oxygen or N—H,-   W particularly preferably represents methyl, ethyl or n-propyl,-   X particularly preferably represents hydrogen, chlorine, bromine,    methyl, ethyl or n-propyl,-   Y particularly preferably represents chlorine, bromine, methyl or    ethyl,    -   with the proviso that at least one of the radicals X or Y        represent halogen,-   A particularly preferably represents C₁-C₆-alkyl, trifluoromethyl,    C₁-C₂-alkoxy-C₁-C₂-alkyl, benzyl, or represents C₃-C₆-cycloalkyl    which is optionally monosubstituted by C₁-C₂-alkyl, C₁-C₂-alkoxy,    fluorine or chlorine,-   B particularly preferably represents hydrogen or C₁-C₂-alkyl,-   A, B and the carbon atom to which they are attached particularly    preferably represent saturated C₅-C₆-cycloalkyl which is optionally    monosubstituted by C₁-C₂-alkyl or trifluoromethyl,-   G particularly preferably represents chlorine, bromine or nitro.-   Q very particularly preferably represents oxygen or N—H,-   W very particularly preferably represents methyl, ethyl or n-propyl,-   X very particularly preferably represents hydrogen, chlorine,    bromine, methyl or ethyl,-   Y very particularly preferably represents chlorine, bromine, methyl    or ethyl,    with the proviso that at least one of the radicals X or Y represents    halogen,-   A very particularly preferably represents methyl, ethyl, n-propyl,    isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl,    trifluoromethyl, benzyl, cyclopropyl, cyclopentyl or cyclohexyl,-   B very particularly preferably represents hydrogen, methyl or ethyl,-   A, B and the carbon atom to which they are attached very    particularly preferably represent saturated C₆-cycloalkyl which is    optionally monosubstituted by methyl,-   G very particularly preferably-represents chlorine or nitro.-   Q especially preferably represents NH,-   W especially preferably represents ethyl or n-propyl,-   X especially preferably represents methyl, ethyl, chlorine or    bromine,-   Y especially preferably represents chlorine, bromine, methyl or    ethyl,    with the proviso that at least one of the radicals X or Y represents    halogen,-   A especially preferably represents methyl, ethyl, n-propyl,    isopropyl, isobutyl, cyclopropyl or benzyl,-   B especially preferably represents hydrogen, methyl or ethyl,-   A, B and the carbon atom to which they are attached especially    preferably represent saturated C₆-cycloalkyl, which is optionally    substituted by methyl,-   G especially preferably represents chlorine.-   Q also especially preferably represents NH,-   W also especially preferably represents methyl or ethyl,-   X also especially preferably represents hydrogen,-   Y also especially preferably represents chlorine or bromine,-   A also especially preferably represents methyl,-   B also especially preferably represents methyl,-   A, B and the carbon atom to which they are attached also especially    preferably represent saturated C₆-cycloalkyl which is optionally    monosubstituted by methyl,-   G also especially preferably represents chlorine.-   Q moreover especially preferably represents oxygen,-   W moreover especially preferably represents methyl or ethyl,-   X moreover especially preferably represents methyl, chlorine or    bromine,-   Y moreover especially preferably represents methyl, bromine or    chlorine,    with the proviso that at least one of the radicals X or Y represents    halogen,-   A, B and the carbon atom to which they are attached moreover    especially preferably represents saturated C₆-cycloalkyl which is    optionally monosubstituted by methyl,-   G moreover especially preferably represents chlorine.

The general or preferred radical definitions or illustrations listedabove can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Thedefinitions apply both to the end products and, correspondingly, toprecursors and intermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Special preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being especially preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, an alkoxy.

Unless indicated otherwise, optionally substituted radicals can be mono-or polysubstituted where, in the case of polysubstitution, thesubstituents can be identical or different.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1) may be specifically mentioned:TABLE 1

A B CH₃ CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇ CH₃ C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃t-C₄H₉ CH₃

CH₃

CH₃

CH₃ —(CH₂)₄— —(CH₂)₅— —CH₂—CHCH₃—(CH₂)₃— —(CH₂)₂—CHCH₃—(CH₂)₂——(CH₂)₂—CHC₂H₅—(CH₂)₂— —CH₂—(CHCH₃)₂—(CH₂)₂—

TABLE 2 A and B are as stated in Table 1 W = C₂H₅; X = C₂H₅; Y = Cl.

TABLE 3 A and B are as stated in Table 1 W = C₂H₅; X = CH₃; Y = Br.

TABLE 4 A and B are as stated in Table 1 W = C₂H₅; X = C₂H₅; Y = Br.

TABLE 5 A and B are as stated in Table 1 W = C₂H₅; X = Br; Y = C₂H₅.

TABLE 6 A and B are as stated in Table 1 W = C₂H₅; X = Cl; Y = Cl.

TABLE 7 A and B are as stated in Table 1 W = C₂H₅; X = Cl; Y = Br.

TABLE 8 A and B are as stated in Table 1 W = C₂H₅; X = Br; Y = Cl.

TABLE 9 A and B are as stated in Table 1 W = C₂H₅; X = Br; Y = Br.

TABLE 10 A and B are as stated in Table 1 W = C₂H₅; X = Cl; Y = CH₃.

TABLE 11 A and B are as stated in Table 1 W = C₂H₅; X = Br; Y = CH₃.

TABLE 12 A and B are as stated in Table 1 W = C₂H₅; X = H; Y = Cl.

TABLE 13 A and B are as stated in Table 1 W = C₂H₅; X = H; Y = Br.

TABLE 14 A and B are as stated in Table 1 W = CH₃; X = CH₃; Y = Cl.

TABLE 15 A and B are as stated in Table 1 W = CH₃; X = CH₃; Y = Br.

TABLE 16 A and B are as stated in Table 1 W = CH₃; X = Cl; Y = CH₃.

TABLE 17 A and B are as stated in Table 1 W = CH₃; X = Br; Y = CH₃.

TABLE 18 A and B are as stated in Table 1 W = CH₃; X = Cl; Y = Cl.

TABLE 19 A and B are as stated in Table 1 W = CH₃; X = Cl; Y = Br.

TABLE 20 A and B are as stated in Table 1 W = CH₃; X = Br; Y = Cl.

TABLE 21 A and B are as stated in Table 1 W = CH₃; X = Br; Y = Br.

TABLE 22 A and B are as stated in Table 1 W = CH₃; X = H; Y = Cl.

TABLE 23 A and B are as stated in Table 1 W = CH₃; X = H; Y = Br.

TABLE 24 A and B are as stated in Table 1 W = C₃H₇; X = Br; Y = Br.

Using, for example, according to process (A),3-[(2-ethyl-4-bromo-6-methyl)phenyl]-5,5-pentamethylenepyrrolidine-2,4-dioneas starting material, the course of the process according to theinvention can be represented by the following reaction scheme:

Using, for example, according to process (B),3-[(2,4-dichloro-6-ethyl)phenyl]-5,5-dimethylpyrrolidine-2,4-dione, thecourse of the process according to the invention can be represented bythe following reaction scheme:

The process (A) is characterized in that compounds of the formula (II)in which A, B, Q, W, X and Y are as defined above are reacted in thepresence of a diluent and a halogenating agent and, if appropriate, afree-radical initiator. Suitable free-radical initiators are, forexample, benzoyl peroxide or azobisisobutyronitrile.

Suitable diluents for use in the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as benzene, toluene and xylene, furthermore ethers,such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl etherand diglycol dimethyl ether, moreover halogenated hydrocarbons, such asdichloromethane, chloroform, carbon tetrachloride, dichloroethane,chlorobenzene, dichlorobenzene, and also esters, such as ethyl acetate.

Suitable halogenating agents for process (A) are, for example, sulphurylchloride, sulphuryl bromide, thionyl chloride, thionyl bromide, imides,such as, for example, N-bromosuccinimide and N-chlorosuccinmide,furthermore chlorosulphonic acid, and also hypochlorites, such as, forexample, tert-butyl hypochlorite.

When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −40° C. and150° C., preferably between 0° C. and 100° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the halogenating agents aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

The process (B) is characterized in that compounds of the formula (II)in which A, B, Q, W, X and Y are as defined above is reacted in thepresence of a diluent and in the presence of a nitrating agent.

Suitable diluents for use in the process (B) according to the inventionare all inert organic solvents. Preference is given to using halogenatedhydrocarbons, such as methylene chloride, chloroform, dichlorobenzeneand dichloroethane.

Suitable nitrating agents are “nitrating acids”, preferably fumingnitric acid.

When carrying out the process (B) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −50° C. and150° C., preferably between 0° C. and 80° C.

The process (B) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (B) according to the invention, thereaction components of the formula (II) and the nitrating agent aregenerally employed in approximately equimolar amounts. However, it isalso possible to use a relatively large excess (up to 5 mol) of onecomponent or the other.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forests, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavourable toxicity to warm-blooded animals. They may preferably beemployed as crop protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhyhchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp;Hemitarsonemus spp., Brevipalpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides ormicrobicides, for example as fungicides, antimycotics and bactericides.If appropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offsets and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on their surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and also their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly disperse silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as sawdust,coconut shells, maize cobs and tobacco stalks; suitable emulsifiersand/or foam-formers are: for example nonionic and anionic emulsifiers,such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and also protein hydrolysates; suitabledispersants are: for example lignin-sulphite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be employed as suchor in their formulations as a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides in order, forexample, to increase the activity spectrum or avoid the development ofresistance. In many cases synergistic effects are achieved, ie. theefficacy of the mixture is greater than the efficacy of the individualcomponents.

Suitable co-components in mixtures are, for example, the followingcompounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole,prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole,propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

-   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,-   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,-   (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,-   (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,-   1-isopropyl    {2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,-   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,-   1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,-   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,-   1-[(diiodomethyl)-sulphonyl]-4-methylbenzene,-   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,-   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,-   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,-   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,-   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,-   2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,-   2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,-   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,-   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,-   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,-   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,-   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,-   2-aminobutane,-   2-bromo-2-(bromomethyl)-pentanedinitrile,-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,-   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,-   2-phenylphenol (OPP),-   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,-   3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,-   3-(1,1-dimethylpropyl)-1-oxo-1H-indene-2-carbonitrile,-   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,-   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,-   4-methyltetrazolo[1,5-a]quinazolin-5(4H)-one,-   8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,-   8-hydroxyquinoline sulphate,-   9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,-   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,-   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethylmorpholine    hydrochloride,-   ethyl [(4-chlorophenyl)-azo]-cyanoacetate,-   potassium bicarbonate,-   methanetetrathiol-sodium salt,-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,-   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,-   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,-   N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,-   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitrobenzenesulphonamide,-   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,-   N-(6-methoxy)-3-pyridinyl-cyclopropanecarboxamide,-   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,-   N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxymethanimidamide,-   N-formyl-N-hydroxy-DL-alanine-sodium salt,-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   O-methyl S-phenyl phenylpropylphosphoramidothioate,-   S-methyl 1,2,3-benzothiadiazole-7-carbothioate,-   spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,-   4-[3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine    Bactericides:    bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulphate and other    copper preparations.    Insecticides/Acaricides/Nematicides:    abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,    aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin,    AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M,    azocyclotin,    Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus    thuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,    bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,    bifenazate, bifenthrin, bioethanomethrin, biopermethrin,    bistrifluron, BPMC, bromophos A, bufencarb, buprofezin, butathiofos,    butocarboxim, butylpyridaben,    cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,    cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,    chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,    chlovaporthrin, chromafenozide, cis-resmethrin, -cispermethrin,    clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,    cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,    cypermethrin, cyromazine,    deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,    diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,    dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,    eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,    esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,    etoxazole, etrimfos,    fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,    fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,    fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,    fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,    flufenoxuron, flumethrin, flutenzine, fluvalinate, fonophos,    fosmethilan, fosthiazate, fubfenprox, furathiocarb,    granulosis viruses,    halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,    hydroprene,    imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion,    ivermectin,    nuclear polyhedrosis viruses,    lambda-cyhalothrin, lufenuron,    malathion, mecarbam, metaldehyde, methamidophos, Metharhizium    anisopliae, metharhizium flavoviride, methidathion, methiocarb,    methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,    mevinphos, milbemectin, milbemycin, monocrotophos,    naled, nitenpyram, nithiazine, novaluron,    omethoate, oxamyl, oxydemethon M,    Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,    propargite, propoxur, prothiofos, prothoate, pymetrozine,    pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion,    pyrimidifen, pyriproxyfen,    quinalphos,    ribavirin,    salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep,    sulprofos,    tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,    teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,    tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid,    thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,    thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,    triarathene, triazamate, triazophos, triazuron, trichlophenidine,    trichlorfon, triflumuron, trimethacarb,    vamidothion, vaniliprole, Verticillium lecanii,    YI 5302,    zeta-cypermethrin, zolaprofos,-   (1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,-   (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,-   1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2-(1H)-imine,-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,-   2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,-   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   3-methylphenyl propylcarbamate,-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzene,-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,-   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,-   Bacillus thuringiensis strain EG-2348,-   [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl    butanoate,-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,-   ethyl    [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,-   N-methyl-N′-(-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,-   N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,-   O,O-diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   N-cyanomethyl-4-trifluoromethyl-nicotinamide,-   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)-propoxy]-benzene.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth regulators.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an excellent residual action on wood andclay as well as by a good stability to alkali on limed substrates.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are understood as meaning plants with novelproperties (“traits”) which are grown by conventional cultivation, bymutagenesis or by recombinant DNA techniques. These may be cultivars,biotypes or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparts particularly advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes), and particular emphasis isgiven to maize, soya beans, potatoes, cotton and oilseed rape. Traitsthat are emphasized are in particular increased defence of the plantsagainst insects by toxins formed in the plants, in particular thoseformed in the plants by the genetic material from Bacillus thuringiensis(for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA,CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof)(hereinbelow referred to as “Bt plants”). Traits which are alsoparticularly emphasized are the increased resistance of plants to fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and the correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylureas, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars having these genetic traits or genetic traits stillto be developed, which cultivars will be developed and/or marketed inthe future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula I orthe active compound mixtures according to the invention. The preferredranges stated above for the active compounds or mixtures also apply tothe treatment of these plants. Particular emphasis is given to thetreatment of plants with the compounds or mixtures specificallymentioned in the present text.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, harvest mites, flies (biting andlicking), parasitic fly larvae, lice, hair lice, feather lice and fleas.These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acaria (Acarina) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100 to10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds according to theinvention have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.Dinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, paper and card, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentsaccording to the invention or mixtures comprising these are to beunderstood as meaning, for example:

building timber, wooden beams, railway sleepers, bridge components, boatjetties, wooden vehicles, boxes, pallets, containers, telegraph poles,wood panelling, wooden windows and doors, plywood, chipboard, joinery orwooden products which are used quite generally in house-building or inbuilding joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations, such as powders, granules, solutions,suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and wood-derived timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic-chemical solventor solvent mixture and/or an oily or oil-like organic-chemical solventor solvent mixture of low volatility and/or a polar organic-chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic-chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum an d/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organic-chemical solvents ofhigh or medium volatility, providing that the solvent mixture likewisehas an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., and that the insecticide/fungicide mixture issoluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic-chemicalsolvent or solvent mixture or an aliphatic polar organic-chemicalsolvent or solvent mixture is replaced. Aliphatic organic-chemicalsolvents containing hydroxyl and/or ester and/or ether groups, such as,for example, glycol ethers, esters or the like, are preferably used.

Organic-chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic-chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic-chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementionedorganic-chemical solvents or diluents, emulsifiers and dispersingagents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing partners are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxideand triflumuron,

and also fungicides, such as epoxyconazole, hexaconazole, azaconazole,propiconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butylcarbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, such as hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells andspecies from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramiumsp., in particular fouling by sessile Entomostraka groups, which comeunder the generic term Cirripedia (cirriped crustaceans), is ofparticular importance.

Surprisingly, it has now been found that the compounds according to theinvention, alone or in combination with other active compounds, have anoutstanding antifouling action.

Using the compounds according to the invention, alone or in combinationwith other active compounds, allows the use of heavy metals such as, forexample, in bis(trialkyltin) sulphides, tri-n-butyltin laurate,tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganeseethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylenebisthiocarbamate, zincoxide, copper(I) ethylenebisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds to be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionallycomprise other active compounds, preferably algicides, fungicides,herbicides, molluscicides, or other antifouling active compounds.

Preferably suitable components in combinations with the antifoulingcompositions according to the invention are:

algicides such as

2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides such as

benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as azaconazole, cyproconazole,epoxyconazole, hexaconazole, metconazole, propiconazole andtebuconazole;

molluscicides such as

fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb andtrimethacarb or conventional antifouling active compounds such as

4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-di-methylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridinetriphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleiimide.

The antifouling compositions used comprise the active compound accordingto the invention of the compounds according to the invention in aconcentration of 0.001 to 50% by weight, in particular 0.01 to 20% byweight.

Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds andinsecticidal active compounds according to the invention, antifoulingpaints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system, in particular in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils such as linseed oil, resin esters or modifiedhardened resins in combination with tar or bitumens, asphalt and epoxycompounds, small amounts of chlorine rubber, chlorinated polypropyleneand vinyl resins.

If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed alone or in combination withother active compounds and auxiliaries in domestic insecticide productsfor controlling these pests. They are active against sensitive andresistant species and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free or passive evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds according to the invention can also be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and areas with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad activity spectrum when used on the soiland on above-ground parts of plants. To a certain extent they are alsosuitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Possible components for the mixtures are known herbicides, for example

acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin(-ethyl), benfuresate, bensulfuron (-methyl), bentazon, benzfendizone,benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox,bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor,butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim,carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben,chloridazon, chlorimuron (-ethyl), chlomitrofen, chlorsulfuron,chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim,clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl),2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P),diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide,flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam,fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn,flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl),flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol,flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron,glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen,haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron,metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

Furthermore suitable for the mixtures are known safeners, for example:

AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D,DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole,fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P),mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example No. I-1-1

At 0-5° C. and under argon, 0.16 ml of sulphuryl chloride (0.002 mol) in3 ml of chloroform is added dropwise to 0.78 g of the compound ofExample I-1-a-53 from EP-A-825 982 (0.002 mol) in 20 ml of anhydrouschloroform. The reaction mixture is heated under reflux for 4 hours. Themixture is then washed twice with in each case 10 ml of NaHCO₃ solution,the filtrate is dried and the solvent is distilled off. The product ispurified by column chromatography on silica gel (dichloromethane:ethylacetate 10:1).

Yield: 0.6 g (71% of theory). M.p. 165° C.

Analogously to Example I-1-1 and in accordance with the generalstatements for the preparation, the following compounds of the formula(I-1) are obtained (I-1)

Ex. No. W X Y A B G m.p. ° C. I-1-2 C₂H₅ H Br CH₃ CH₃ Cl 160 I-1-3 C₂H₅C₂H₅ Br CH₃ CH₃ Cl 164 I-1-4 C₂H₅ Cl Cl CH₃ CH₃ Cl 120 I-1-5 C₂H₅ CH₃ Bri-C₃H₇ CH₃ Cl oil I-1-6 C₂H₅ CH₃ Cl CH₃ CH₃ Cl 130 I-1-7 C₃H₇ Br Br CH₃CH₃ Cl 172 I-1-8 C₂H₅ Cl Br CH₃ CH₃ Cl 132 I-1-9 C₂H₅ Br Cl CH₃ CH₃ Cl145 I-1-10 C₂H₅ Br CH₃ CH₃ CH₃ Cl oil I-1-11 C₂H₅ Br CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— Cl 212 I-1-12 C₂H₅ Br Br —(CH₂)₂—CHCH₃—(CH₂)₂— Cl209 I-1-13 C₂H₅ C₂H₅ Cl —(CH₂)₂—CHCH₃—(CH₂)₂— Cl 210 I-1-14 C₂H₅ Br Cl—(CH₂)₂—CHCH₃—(CH₂)₂— Cl 220 I-1-15 C₂H₅ C₂H₅ Br —(CH₂)₂—CHCH₃—(CH₂)₂—Cl 214 I-1-16 C₂H₅ CH₃ Cl —(CH₂)₂—CHCH₃—(CH₂)₂— Cl 206 I-1-17 C₃H₇ Br Br—(CH₂)₂—CHCH₃—(CH₂)₂— Cl 217 I-1-18 C₂H₅ H Br —(CH₂)₂—CHCH₃—(CH₂)₂— Cl182 I-1-19 C₂H₅ CH₃ Br —(CH₂)₂—CHCH₃—(CH₂)₂— Cl 225 I-1-20 C₂H₅ Cl Cl—(CH₂)₂—CHCH₃—(CH₂)₂— Cl 230 I-1-21 C₂H₅ Br CH₃ —(CH₂)₅— Cl 154 I-1-22C₂H₅ Br CH₃

CH₃ Cl foam I-1-23 C₂H₅ Br CH₃ C₂H₅ C₂H₅ Cl 158-164 I-1-24 C₂H₅ Br CH₃C₃H₇ CH₃ Cl oil I-1-25 C₂H₅ C₂H₅ Br i-C₃H₇ CH₃ Cl oil I-1-26 C₂H₅ C₂H₅Br —(CH₂)₅— Cl 211 I-1-27 C₂H₅ C₂H₅ Br CH₃ H Cl wax I-1-28 C₂H₅ C₂H₅ BrC₆H₅—CH₂ H Cl 139 I-1-29 C₂H₅ C₂H₅ Br i-C₃H₇ H Cl 135 I-1-30 C₂H₅ C₂H₅Br i-C₄H₉ H Cl 144 I-1-31 C₂H₅ CH₃ Br CH₃ CH₃ Cl  91 I-1-32 C₂H₅ CH₃ BrCH₃ H Cl oil I-1-33 C₂H₅ CH₃ Br C₆H₅CH₂ H Cl oil I-1-34 C₂H₅ CH₃ Bri-C₄H₉ H Cl 117 I-1-35 C₂H₅ CH₃ Br —(CH₂)₅— Cl 188 I-1-36 C₂H₅ Br Br—(CH₂)₅— Cl oil I-1-37 C₂H₅ Br Br i-C₃H₇ H Cl oil I-1-38 C₂H₅ Cl Cl—(CH₂)₅— Cl 181 I-1-39 C₂H₅ Cl Br —(CH₂)₅— Cl 192 I-1-40 C₂H₅ Cl Br—(CH₂)₂—CHCH₃—(CH₂)₂— Cl 226 I-1-41 C₂H₅ Br Cl —(CH₂)₅— Cl 155

Example I-2-1

0.982 g (3.0 mmol) according to Ex. No. I-2-a-1 (WO 96/35664) isdissolved in 30 ml of tetrahydrofuran, 0.358 g (3.30 mmol) of tert-butylhypochlorite is added dropwise and the mixture is stirred at roomtemperature for 6 h and concentrated using a rotary evaporator. Thecrude product is purified by column chromatography on silica gel (mobilephase dichloromethane).

Yield: 0.90 g (75% of theory), m.p. 108-110° C.

Analogously to Example I-2-1 and in accordance with the generalstatements for the preparation, the following compounds of the formula(I-2) are obtained (I-2)

Ex. No. W X Y A B G m.p. ° C. I-2-2 CH₃ CH₃ Br —(CH₂)₅— Cl 123-125 I-2-3CH₃ Br CH₃ —(CH₂)₅— Cl  98-100 I-2-4 CH₃ Cl CH₃ —(CH₂)₅— Cl 120-122I-2-5 C₂H₅ CH₃ Br —(CH₂)₅— Cl *1.25 (t, 3H, CH₂CH₃) 2.40 (s, 3H, ArCH₃)I-2-6 CH₃ Br Br —(CH₂)₅— Cl 118-120 I-2-7 CH₃ CH₃ Cl —(CH₂)₅— Cl 95I-2-8 CH₃ Cl Br —(CH₂)₅— Cl 88-90 I-2-9 C₂H₅ Br CH₃ —(CH₂)₅— Cl *1.35(t, 3H, CH₂CH₃) 2.35 (s, 3H, Ar—CH₃)*¹H-NMR (400 MHz, CDCl₃): shifts δ in ppm.

USE EXAMPLES Example A

Post-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants of a height of 5-15 cm are sprayed with the preparation ofactive compound such that the particular amounts of active compounddesired are applied per unit area. The concentration of the spray liquoris chosen such that the particular amounts of active compound desiredare applied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction

Example B

Pre-Emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sewn in normal soil. After about 24 hours,the soil is sparyed with the preparation of active compound such thatthe particular amounts of active compound desired are applied per unitarea. The concentration of the spray liquor is chosen such that theparticular amounts of active compound desired are applied in 1000 l ofwater/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control.

The figures denote:

0%=no effect (like untreated control)

100%=total destruction post-emergence g ai/ha Sugar beet AlopecurusAvena fatua Echinochloa Setaria Ex. I-1-2 250 0 95 100 100 100 Ex. I-1-3250 0 95 100 100 95 pre-emergence g ai/ha Alopecurus Avena fatuaEchinochloa Setaria Ex. I-1-3 250 100 95 100 100

Example C

Meloidogyne Test

Solvents:

-   -   78 parts by weight of acetone    -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Vessels are filled with sand, solution of active compound, Meloidogyneincognita egg/larvae suspension and lettuce seeds. The lettuce seedsgerminate and the plants develop. On the roots, galls develop.

After the desired period of time, the nematicidal action is determinedin % by the formation of galls. 100% means that no galls have beenfound; 0% means that the number of galls on the treated plantscorresponds to that of the untreated control.

In this test, for example, the following compounds of the PreparationExamples show good activity: TABLE C Plant-damaging nematodesMeloidogyne test Active Concentration of active Effect in % compoundscompound in ppm after 14^(d) Ex. I-1-3 20 100 Ex. I-1-1 20 100

Example D

Tetranychus Test (OP-Resistant/Spray Treatment)

Solvents:

-   -   78 parts by weight of acetone    -   1.6 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of the leaves of beans (Phaseolus vulgaris) which are infested byall stages of the greenhouse red spider mite (Tetranychus urticae) aresprayed with a preparation of active compound of the desiredconcentration.

After the desired period of time, the activity in % is determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites have been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity: TABLE D Plant-damaging mites Tetranychustest (OP-resistant/spray treatment) Active Concentration of active Killrate in % compound compound in ppm after 4^(d) Ex. I-1-2 100 80 Ex.I-1-3 100 80 Ex. I-1-1 100 80

Example E

In vitro test for the ED₅₀ determination in microorganisms

A methanolic solution of the active compound to be tested, admixed withemulsifier PS16 is pipetted into the wells of microtiter plates. Afterthe solvent has evaporated, 200 μl of potato/dextrose medium are addedto each well.

Beforehand, a suitable concentration of spores or mycelium of the fungusto be tested was added to the medium.

The resulting concentrations of the active compound are 0.1, 1, 10 and100 ppm. The resulting concentration of the emulsifier is 300 ppm.

The plates are then incubated on a shaker at a temperature of 22° C. for3-5 days, until sufficient growth can be observed in the untreatedcontrol.

Evaluation is carried out photometrically at a wavelength of 620 nm. Thedose of active compound which causes 50% inhibition of fungal growthcompared to the untreated control (ED₅₀) is calculated from the datameasured at different concentrations. TABLE E In vitro test for the ED₅₀determination in microorganisms Active compound Microorganisms ED₅₀value Ex. I-1-2 Rhizoctonia solani 2.04 Ex. I-1-3 Rhizoctonia solani1.37 Ex. I-1-1 Rhizoctonia solani 1.66

Example F

Plasmopara Test (Grapevine)/Protective

Solvents: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 1 day. Theplants are then placed in a greenhouse at about 21° C. and about 90%atmospheric humidity for 4 days. The plants are then moistened andplaced in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corrresponds to that of the control, whereas an efficacyof 100% means that no infection is observed. TABLE F Plasmopara test(grapevine)/protective Application rate of active Active compoundcompound in g/ha efficacy in % Ex. I-1-2 750 87 Ex. I-1-3 750 75

Example G

Critical Concentration Test/Soil Insects—Treatment of Transgenic Plants

Test insect: Diabrotica balteata—larvae in soil

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is poured onto the soil. Here, theconcentration of the active compound in the preparation is virtuallyimmaterial, only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l), matters. The soil is filled into0.25 l pots, and these are allowed to stand at 20° C.

Immediately after the preparation, 5 pregerminated maize corns of thecultiva YIELD GUARD (trademark of Monsanto Comp., USA) are placed intoeach pot. After 2 days, the appropriate test insects are placed into thetreated soil. After a further 7 days, the efficacy of the activecompound is determined by counting the maize plants that have emerged (1plant=20% activity).

Example H

Heliothis Virescens Test—Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soyabean shoots (Glycine max) of the cultiva Roundup Ready (trademark ofMonsanto Comp. USA) are treated by being dipped into the preparation ofactive compound of the desired concentration and are populated with thetobacco budworm Heliothis virescens while the leaves are still moist.

After the desired period of time, the kill of the insects is determined.

1-13. (canceled)
 14. A compound of formula (I)

in which Q represents oxygen or N—H, W represents alkyl, X representshydrogen, halogen, or alkyl, Y represents halogen or alkyl, with theproviso that at least one of the radicals X or Y represents halogen, Arepresents haloalkyl, alkyl, alkoxyalkyl or optionally substitutedcycloalkyl, B represents hydrogen or alkyl, or A and B together with thecarbon atom to which they are attached represent a optionally alkyl- orhaloalkyl-substituted saturated cycle, and G represents halogen ornitro.
 15. A compound of formula (I) according to claim 14 in which Qrepresents oxygen or N—H, W represents C₁-C₄-alkyl, X representshydrogen, halogen, or C₁-C₄-alkyl, Y represents halogen or C₁-C₂-alkyl,with the proviso that at least one of the radicals X or Y representshalogen, A represents C₁-C₈-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, or benzyl; or represents C₃-C₆-cycloalkyl thatis optionally mono- or disubstituted by C₁-C₄-alkyl, C₁-C₄-alkoxy, orhalogen, B represents hydrogen or C₁-C₄-alkyl, or A, B, and the carbonatom to which they are attached represent saturated C₃-C₈-cycloalkylthat is optionally mono- or disubstituted by C₁-C₄-alkyl orC₁-C₂-haloalkyl, and G represents chlorine, bromine, or nitro.
 16. Acompound of formula (I) according to claim 14 in which Q representsoxygen or N—H, W represents methyl, ethyl, or n-propyl, X representshydrogen, chlorine, bromine, methyl, ethyl, or n-propyl, Y representschlorine, bromine, methyl, or ethyl, with the proviso that at least oneof the radicals X or Y represents halogen, A represents C₁-C₆-alkyl,trifluoromethyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, or benzyl; or representsC₃-C₆-cycloalkyl that is optionally monosubstituted by C₁-C₂-alkyl,C₁-C₂-alkoxy, fluorine, or chlorine, B represents hydrogen orC₁-C₂-alkyl, or A, B, and the carbon atom to which they are attachedrepresent saturated C₅-C₆-cycloalkyl that is optionally monosubstitutedby C₁-C₂-alkyl or trifluoromethyl, and G represents chlorine, bromine,or nitro.
 17. A compound of formula (I) according to claim 14 in which Qrepresents oxygen or N—H, W represents methyl, ethyl, or n-propyl, Xrepresents hydrogen, chlorine, bromine, methyl or ethyl, Y representschlorine, bromine, methyl, or ethyl, with the proviso that at least oneof the radicals X or Y represents halogen, A represents methyl, ethyl,n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl,trifluoromethyl, benzyl, cyclopropyl, cyclopentyl, or cyclohexyl, Brepresents hydrogen, methyl, or ethyl, or A, B, and the carbon atom towhich they are attached represent saturated C₆-cycloalkyl that isoptionally monosubstituted by methyl, and G represents chlorine ornitro.
 18. A compound of formula (I) according to claim 14 in which Qrepresents NH, W represents ethyl or n-propyl, X represents methyl,ethyl, chlorine, or bromine, Y represents chlorine, bromine, methyl, orethyl, with the proviso that at least one of the radicals X or Yrepresents halogen, A represents methyl, ethyl, n-propyl, isopropyl,isobutyl, cyclopropyl, or benzyl, B represents hydrogen, methyl, orethyl, or A, B, and the carbon atom to which they are attached representsaturated C₆-cycloalkyl that is optionally substituted by methyl, and Grepresents chlorine.
 19. A compound of formula (I) according to claim 14in which Q represents NH, W represents methyl or ethyl, X representshydrogen, Y represents chlorine or bromine, A represents methyl, Brepresents methyl, or A, B, and the carbon atom to which they areattached represent saturated C₆-cycloalkyl that is optionallymonosubstituted by methyl, and G represents chlorine.
 20. A compound offormula (I) according to claim 14 in which Q represents oxygen, Wrepresents methyl or ethyl, X represents methyl, chlorine, or bromine, Yrepresents methyl, bromine, or chlorine, with the proviso that at leastone of the radicals X or Y represents halogen, A, B, and the carbon atomto which they are attached represent saturated C₆-cycloalkyl that isoptionally monosubstituted by methyl, and G represents chlorine.
 21. Aprocess for preparing a compound of formula (I) according to claim 14comprising (A) for compounds of formulas (I-1) to (I-2)

in which A, B, Q, W, X, and Y are as defined for formula (I) of claim14, and G represents halogen,  reacting a compound of formulas (II-1) to(II-2)

in which A, B, Q, W, X, and Y are as defined for formula (I) of claim14, with a halogenating agent in the presence of a solvent and,optionally, in the presence of a free-radical initiator, or (B) forcompounds of formulas (I-1) to (I-2)

in which A, B, Q, W, X, and Y are as defined for formula (I) of claim14, and G represents nitro,  reacting a compound of formulas (II-1) to(II-2)

in which A, B, Q, W, X, and Y are as defined for formula (I) of claim14, with a nitrating agent in the presence of a solvent.
 22. A processaccording to claim 21 wherein the nitrating agent of alternative (B) isfuming nitric acid.
 23. A pesticide or herbicide composition comprisingone or more compounds of formula (I) according to claim 14 and one ormore extenders and/or surfactants.
 24. A method for controlling animalpests comprising allowing an effective amount of one or more compoundsof formula (I) according to claim 14 to act on animal pests and/or theirhabitat.
 25. A method for controlling unwanted vegetation comprisingallowing an effective amount of one or more compounds of formula (I)according to claim 14 to act on unwanted vegetation and/or its habitat.26. A process for preparing a pesticide or herbicide compositioncomprising mixing one or more compounds of formula (I) according toclaim 14 with one or more extenders and/or surfactants.